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SMB00370

Sigma-Aldrich

Tetrahydrocurcumin

≥96% (HPLC)

Sinónimos:

Tetrahydrocurcumin, 1,7-bis(4-hydroxy-3-methoxyphenyl)-3,5-heptanedione, HZIV 81-2, NSC687845, Tetrahydrodiferuloylmethane, 1,7-Bis(4-hydroxy-3-methoxyphenyl)-3,5-heptanedione

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About This Item

Fórmula empírica (notación de Hill):
C21H24O6
Número de CAS:
36062-04-1
Peso molecular:
372.41
Beilstein/REAXYS Number:
3485469
MDL number:
MFCD04152347
UNSPSC Code:
12352205
PubChem Substance ID:
329824974
NACRES:
NA.25

Quality Level

200

assay

≥96% (HPLC)

form

powder

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

SMILES string

COc1cc(CCC(=O)CC(=O)CCc2ccc(O)c(OC)c2)ccc1O

InChI

1S/C21H24O6/c1-26-20-11-14(5-9-18(20)24)3-7-16(22)13-17(23)8-4-15-6-10-19(25)21(12-15)27-2/h5-6,9-12,24-25H,3-4,7-8,13H2,1-2H3

InChI key

LBTVHXHERHESKG-UHFFFAOYSA-N

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General description

Tetrahydrocurcumin (THC) is a colorless metabolite of curcumin. It has a similar structure to that of curcumin. THC lacks the α, β-unsaturated carbonyl moiety in its chemical structure. It is naturally sourced from the roots of Curcuma zedoaria, Zingiber mioga, and Zingiber officinale.

Application

Tetrahydrocurcumin (THC) has been used as a neuroprotective agent to study its therapeutic potential in improving mitochondrial dysfunction in the ischemic stroke mice model.

Biochem/physiol Actions

Tetrahydrocurcumin is well-studied in treating cancer for its excellent anti-cancer, anti-angiogenic, and chemopreventative activities. It also exerts anti-inflammatory properties. Tetrahydrocurcumin has been shown to have antioxidant and protective effects against diabetes, and vascular dysfunction via alleviation of oxidative stress.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

385.2 °F

flash_point_c

196.2 °C

Certificados de análisis (COA)

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Sunmin Park et al.
Genes & nutrition, 11, 2-2 (2016-08-03)
Menopausal symptoms are associated with inflammation. Curcumin is a well-known anti-inflammatory bioactive compound from turmeric whereas tetrahydrocurcumin (THC) is a major metabolite of curcumin that may have different efficacies. However, they have not been studied for anti-menopausal symptoms and anti-osteoarthritis
Pidaran Murugan et al.
Life sciences, 79(18), 1720-1728 (2006-06-30)
Oxidative stress has been suggested to be a contributory factor in development and complication of diabetes. In the present study, we have investigated the effect of tetrahydrocurcumin (THC), one of the active metabolites of curcumin on antioxidants status in streptozotocin-nicotinamide
Ching-Shu Lai et al.
Biomolecules, 10(6) (2020-06-04)
In recent decades, cancer has been one of the leading causes of death worldwide. Despite advances in understanding the molecular basis of tumorigenesis, diagnosis, and clinical therapies, the discovery and development of effective drugs is an active and vital field
Upa Kukongviriyapan et al.
The Tohoku journal of experimental medicine, 239(1), 25-38 (2016-05-07)
Cadmium (Cd) is a non-essential heavy metal with high toxicity potential. Humans are exposed to Cd present in diet, polluted air, and cigarette smoke. Cd exposure has been associated with increased risk of chronic diseases, including hypertension, atherosclerosis, diabetes, and
Pornprom Yoysungnoen et al.
World journal of gastroenterology, 14(13), 2003-2009 (2008-04-09)
To determine the effect of tetrahydrocurcumin (THC) on tumor angiogenesis compared with curcumin (CUR) by using both in vitro and in vivo models of human hepatocellular carcinoma cell line (HepG2). The 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-tetrazolium bromide (MTT) assay was used for testing the
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